Tert-Butylamine → (S)-[2-(4-benzyloxy-phenyl)-1-tert-butylcarbamoyl-ethyl]-carbamic acid tert-butyl ester
Reaction equation
[NH2:1][C@@H:2]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)[C:3]([NH:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[C:25](N[C@H](C(O)=O)CC1C=CC(OCC2C=CC=CC=2)=CC=1)([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].C(N(C(C)C)CC)(C)C.C(N)(C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[C:28]([O:27][C:25](=[O:26])[NH:1][C@H:2]([C:3](=[O:4])[NH:5][C:6]([CH3:7])([CH3:9])[CH3:8])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:16]=1)([CH3:31])([CH3:30])[CH3:29]Participants
8
Reactant 5
HCID 6385Tert-Butylamine
HCID 81531Diisopropylethylamine
HCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosine
HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 15517727(S)-2-amino-3-(4-benzyloxy-phenyl)-N-tert-butyl-propionamideProduct 1
Reagents, catalysts & solvents 2
Procedure
The Preparation of (S)-2-Amino-3-(4-benzyloxy-phenyl)-N-tert-butyl-propionamide (Ia) ##STR26## Step i: N-Boc-O-Benzyl-tyrosine (20.0 g, 53.9 mmol) was dissolved in DMF (270 mL) and treated with diisopropylethylamine (19 mL, 108 mmol), tert-butylamine (5.7 mL. 53.9 mmol), and HBTU (13.9 g, 53.9 mmol). The reaction was stirred for 15 minutes and then diluted with EtOAc (1 L), washed with saturated bicarbonate solution (2×1 L) and brine (1 L), dried over Na2SO4 and concentrated to give 22.1 g (92%) of (S)-[2-(4-benzyloxy-phenyl)-1-tert-butylcarbamoyl-ethyl]-carbamic acid tert-butyl ester.
Workup
- washwashed with saturated bicarbonate solution (2×1 L) and brine (1 L)
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-9d63494014904f20bda0e7f61410eeea
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06117841
Reaction notes
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